


In the middle of the night.

by Gothgirl35023



Category: Supernatural
Genre: Anal Sex, Basically smutty sex between Dean and Crowley, Bottom Dean, But he denies it, Crowley's a dick, Crowley's smug, Dean in Panties, Dean is willing, Forced Feminization, Lingerie, M/M, Not a whole lot of plot, Rimming, Top Crowley
Language: English
Status: Completed
Published: 2016-05-21
Updated: 2016-05-21
Packaged: 2018-06-09 17:20:19
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,507
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6916396
Author URL: https://archiveofourown.org/users/Gothgirl35023/pseuds/Gothgirl35023
Summary: <blockquote class="userstuff">
              <p>When Sam goes to sleep, Dean's sneaking out and joining his secret, not lover, but they're in bed together, with hatred and a mind numbing orgasm.</p>
            </blockquote>





	In the middle of the night.

**Author's Note:**

> Not totally sure why I did this.. but for me, there's only few that Dean's gonna bottom for and one of them is Crowley. There's no really set time line for this.

"My, my, squirrel." Crowley's smooth, rich voice filled his ears. Which was pounding with blood, his stomach twisting in a sharp knot. The King of Hell just chuckled lightly. "What would your brother think if he saw you.. just in front of me like this.." He purred.

"Shut up." Dean gnashed his teeth together, glaring at the King before him. King, indeed. King of jackasses was more like that. He couldn't dare to let Sam even have this image in his head. Of how Dean was, how he looked. ANY of it. The moment he knew Sam was fast asleep, really fast asleep, Dean gathered up his things and bolted out of their hotel, heading for this destination.

A much nicer hotel then the little fleabag motel the brothers had entertained to stay at. Cheap, effective. That was their way of life. Ya know.. but this hotel? Holy shit. Dean nearly pissed him when he was walking in, almost afraid someone was going to toss him out on his ass for the way he looked. But they didn't give him a second glance. And he took the room key right up to the floor, to the room.

Room? Fucking suite.

Wine, chocolates.. everything. It was in the god damned suite and Dean wanted to explore it a little more. Fuck, looking at the prices for room service made him feel like a pauper. But.. there was no time to really waste. Time to get going. He took the items from the bag and walked to the bathroom now.

Back to the present.. where Crowley found him, splayed out on the large bed, which was covered in silky black and red sheets, even the pillows.. Dean swallowed thickly, fighting off the flush from his face as the eyes examined him. Stared right through him it seemed. Crowley chuckled lightly. "Oh, there's no need to be so shy, Dean.." He murmured. "Such a lovely woman you make.."

"Shut the fuck UP."

Finding the outfit was somehow the easiest part, where Dean was covered in so much shame as he moved around the bed. Crowley chuckled once more, taking a sip from the glass in his hand as he took his time to thoroughly examine the outfit his new lovely had on. Utterly lovely.

He was wondering how on earth Dean might be able to walk in those high heels.. Both leading up to lacy black stockings that covered his legs, which Crowley noticed, his legs appeared to be shaved. He decided not to comment and his eyes trailed higher as those stockings stopped thigh-high. Dean's cheeks flushed to red, turning his own eyes away as he felt demonic ones take in the sight of the panties. The panties were black with fucking red ruffles all over them, that did nothing to hide his cock, which was betraying him by poking out of the top of the panties. Fuck.

Finally, Crowley's eyes came to the last piece of the outfit. A lovely little red see through camisole. "Mm. It is a lovely sight to see, Deanna." The female name had Dean stuttering and regaining some of voice to curse at the Demon. "Fuck you!" He snarled, though it was lost in Crowley's chuckle. Fuck, fuck. FUCK.

'Oh, in good time, you'll be the one fucked, squirrel.'

Such a mouth on the boy. Soon that mouth would be put to a much better use in Crowley's opinion. He simply hummed and set the glass of scotch aside. "Get on your hands and knees, Dean. Turn around for me and let me see."

Fuck, fuck. FUCK. Dean wanted to disobey, to duck his head and run away in shame, tail between his legs. He was Dean Winchester and he bowed to no one! But... he had promised to obey. To obey Crowley, whatever his orders were. Even this.. slowly, he shifted around and pushed up on his knees, crawling around, his head forced down as his cheeks were so red, he felt like he could die of shame, until he was facing the headboard with his ass right out on display. God..

God, indeed. Seemed the man created such lovely things for Crowley.. The raven haired demon smirked lightly, his eyes taking in the line, the plump of Dean Winchester's arse. "God, you two.. you and your brother. Loveliest little things I've ever seen," He murmured and almost giggled, watching Dean's back stiffen.

"Don't fucking mention Sam here," Dean snarled the order in a low voice, keeping his eyes forward. Crowley's eyebrows rose, but for the moment, he decided to let that go. "Moose, hmm? I can only imagine what Moose would say? What he'd do.. seeing his brother dressed like some filthy slut for the KING of Hell, don't you think?"

Dean tried not to, but he fucking shivered at the way Crowley said he was a slut. He felt like a slut, like a damned whore. Perched like this, exposed.. and it wasn't going to end there.. To his surprise, a sudden gasp escaped him as strong, rough hands gripped handfuls of his ass and squeezed. "Lovely."

Such a plump thing in his grasp. Dean shifted a bit at the light squeezes, trying to keep himself rounded. Trying NOT to think about how he liked his ass grabbed.. fuck.. "Fuck.." He breathed softly. His hips arched just the slightest as the hands moved to tug the panties down now. "Hey, wait a second." He protested. "What.. what are you."

"Hush." The demon ordered. This was a beautiful little gift and he wasn't about to just allow Dean to take it all away, due to some sudden shyness. "Eyes forward, Dean.. you'll see in a moment. That's my good boy.." He pulled the flimsy fabric down to his thighs, catching with the stockings. "Mm.." Once more, Dean gasped as those skillful hands squeezed his cheeks, pulling them apart.

Crowley practically licked his lips, eyeing the puckered entrance. How lovely.. pink and delicious. "Such a pretty little cunt, you have, Deanna.." Dean dropped his head again, pressing it against the sheets, miserably. Stupid.. "S.. Stop it, Crowley.." His cock was aching already, almost hard as a rock, it seemed and leaking, bobbing between his legs. He hated himself so much..

Yes, okay! Dean liked being dressed up like some painted whore, having someone telling him what to do. Orders in bed, sometimes.. Hell, he let a woman spank him once, wore her panties.. which were amazing silk.. and now, here he was with Crowley's fucking hands on his ass and a tongue.. oh, god..

Dean gasped, arching upward a bit as the tongue swiped across his entrance, taking a long lick. Behind him, he heard the hum as Crowley licked him again. Taking his sweet time to lick across his hole, laving saliva across the pucker, tasting his Winchester. And he found it delicious. Crowley licked at his hole, sliding his head down a bit to continue. Up and down, he licked at the slicking spot. "Mmn.. nnm.." It was like a man savoring the first taste of water in forever.

Making noises and Dean made a few right with him.. "Fuck.. fuck.." Oh, god, yeah.. He pushed up on his hands, pushing his ass out a little bit. That tongue was licking over his balls, Crowley's hands gripping his hips, TIGHT. Just to keep him from squirming to much. "C.. Crowley, fuck." He swore miserably. "C'mon, don't.. uhmmmm..!" Felt too good... amazing.. Okay, so he was a slut for sex as well.. He panted a bit, his limbs quivering just a bit as he was given a most amazing rimming of his life. "Mnn.."

Crowley took one final last lick, savoring the taste for a moment. Taking his head away, he licked his lips. "My, Deanna.. you taste so wonderful for your daddy." He leaned up a bit, taking hold of Dean's hips once more. Dean gasped aloud as in that sudden movement, he was flipped over and onto his back. Now, Crowley perched above him, never looking rumpled in his expensive, Dean probably couldn't pronounce the name clothing. Fucking prick..

The hunter groaned softly, turning his head to the side as Crowley attempted to kiss him. No.. "No. You don't fucking kiss me." He grunted. He didn't want that.. as much as his throbbing dick protested, bobbing against the camisole and smearing precum on the fabric. "Ge..."

"Get off?" Crowley teased, perching himself careful. He wanted to see it all.. to see his lovely Winchester become a frustrated sobbing mess. "We'll get to that soon, my dear.." His hand slipped its way downward, fingers grasping around his cock. "Such a monster, Dean.. but mine's much bigger." He taunted lightly. Dean hated his body for the way his cock twitched, his hole twitching with the idea of having Crowley inside of him, pounding deep until he exploded.

"M'not a fucking bottom.." Dean did try to protest, shoving at the man's chest above him. Another groan escaped him as the chance was taken and Crowley forced a deep kiss onto his mouth. Easily, a sneaky tongue slipped in and Dean nearly choked as it practically wrapped around his. His hands fisted in the dark jacket, pulling the demon right to him as they kissed. Kissed, nearly butted heads.. something..

"Fucking DICK." Dean swore, spit dripping down his chin as the kiss was broken. Crowley nearly chuckled at the harsh insult against his lips. Such a sassy little thing.. and so easy to move. "If you're gonna fuck me, why don't you do it and now." He demanded. Sassy, sassy..

"Oh, not yet."

"H.. Hey!" Dean snapped angrily, his wrists suddenly forced up and now bound against the headboard with the expensive silk tie Crowley had loosened from his neck. What the FUCK. It wasn't coming loose either. He tilted his head back, chest heaving lightly as he glared at the man before him, the bastard. "Untie me!"

"I think not," Crowley decided. He pushed himself calmly off of the bed and began to undo the buttons of his jacket. Once the two were gone and done, he took his time then to unbutton his shirt. Where he saw Dean was starting to clench his teeth in annoyance. He was hard as a rock and Crowley hadn't fucked him, yet. He wanted Dean to suffer it soon. "You fucking.."

"Language, Deanna.. you'll have it soon enough," The King of Hell climbed back onto the bed, brushing a finger, a single finger across Dean's chest, the fabric rustling so softly. "Mm.. you are quite the lovely angel in red, Deanna.." He leaned down, running his lips over his chest through the silk. "I love this.." He breathed. "These.." Dean nearly jumped out of his skin, a soft moan escaping him as the lips and teeth bit at his nipple through the fabric. "Fuck.."

Crowley groaned himself as the jerking hips pushed against his own. "Patience.." He murmured. Almost a bit eagerly, he bit at the hardening nipple once more, taking his time to pull. As he did, his hand drifted down and lazily wrapped around the aching shaft. "My.. so hard. Your perky nipples, darling.." No, No..

Dean hissed underneath him, letting his head thump back against the pillows on the bed. God.. "Crowley.. Crowley.. come on!" Damn it, he felt like he was going to explode.. if he didn't get something good already..

It didn't take much. Dean gasped for air, his back arching as the fingers drove into him. Pushing against the bundle of nerves that would drive him wild and it did. Fucking Crowley knew exactly what he was doing, the bastard. "Come on.. come on, fuck me already.." At that point, skin slick with sweat and his cock throbbing full of need, Dean truly didn't care how he sounded. He just wanted SOMETHING inside of him, bigger then fingers.

Crowley licked his lips a bit, a little smirk on his face. Such a pretty boy for him.. "Patience, my pet.." He removed his fingers, amused by how wet they were. Tease a boy enough and he'd fall right to pieces. Just the way he wanted him.. "That's my good boy.. let's see what I can do for you.." He probably wouldn't even need lube and he wouldn't use any either.

Behind the Winchester, he placed a hand on Dean's lower back, having brought him back around on his hands and knees. Patience, indeed. Dean was never one to be patient. "C'mon, old man.." He growled lightly. Taunting him.. "Stick it inside.. or are you LIMP?" He chuckled to himself. Limp, hmm?

"Such a mouth.." If Dean desired to be a little brat, then he wouldn't have anything good coming to him.. Crowley worked his hand over his hard cock, the tip of it just brushing against the rim. So tight, actually.. and soon, it would be wrecked. Wrecking Dean Winchester.

"Come on, Crowley. I-fuck!" Dean swore and Crowley near preened in amusement. That was exactly what he wanted to hear. "Limp, hmm? Oh no, Dean. Far from it.." His voice was a damned deep purr as the King seated himself fully inside of Dean's tight ass. His fingers gripped his hips still. Crowley pulled out, just a bit, thrusting back inside.

Dean's fingers curled into fists once again, still bound by the tie. He dropped his head against the pillow, gasping as the cock pushed deeper inside of him. God, it felt like he was being turned inside out by the act. "A.. Ah, fuck.." He swore. "C'mon.." Yes.. On his hands and knees, being fucked by his enemy.. his fucking enemy.. moving into him and pounding away like he was a paid whore.

Crowley leaned forward, dropping his head to whisper in his ear. "Won't take much, will it, Dean?" His fingers skimmed the edges of the lace stockings, teasing. "A little more and I'll have you turned upside the down.."

"Fuck.. you!"

Fuck, indeed. Crowley hummed, skimming his lips along the side of Dean's neck, tongue sliding out to lick the salty skin. So delicious.. Dean gasped underneath him, twisting himself as best as he could in his position. His hips were banging against the hunter's ass, over and over, in that fast rhythm that had the demon aching and Dean panting for air. "Nnm! Fuck!"

"Uhm.." Dean was drooling, gasping as he rocked back. He'd hate himself in the morning, right after this. He didn't even need to be touched, before he came, cock sputtering and leaking onto the sheets below. Such a tight ass.. Seemed to tighten further around Crowley and the demon thrust a few more times, cumming INSIDE of Dean.

The room was silent for the moment, Dean closing his eyes and trying to breathe through his nose. "Now.. was that so terrible, pet?" Crowley murmured, laughing now as Dean twisted his head, glaring at him. "I.. fuckin'.. hate your ass, Crowley.."

"Oh, I know you do, darling. But I just came in YOURS."

**Author's Note:**

> I would totally take requests. For pairings or AU's.. for the Supernatural verse.. I like to write.


End file.
